N-Methyltaurine

Last updated
N-Methyltaurine
N-Methyl taurine Structure V.1.svg
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.192 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-510-3
PubChem CID
UNII
  • InChI=1S/C3H9NO3S/c1-4-2-3-8(5,6)7/h4H,2-3H2,1H3,(H,5,6,7)
    Key: SUZRRICLUFMAQD-UHFFFAOYSA-N
  • CNCCS(=O)(=O)O
Properties
C3H9NO3S
Molar mass 139.17 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H314, H315, H319
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Methyltaurine (2-methylaminoethanesulfonic acid) is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents (just like amino acids). [1] In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae, [2] where it is formed by methylation of taurine. It is suitable for esterification (actually amide formation) with long-chain carboxylic acids to taurides (acylaminoethansulfonaten) because of its high polarity and the relatively good solubility of its alkaline earth metal salts, which are also used as mild anionic surfactants. [3]

Contents

Preparation

The synthesis of N-methyltaurine was reported as early as 1878, [4] with methylamine being reacted with the silver salt of 2-chloroethanesulfonic acid. An obvious modification for this reaction is the replacement of the silver salt of 2-chloroethanesulfonic acid by the sodium salt of 2-chloroethanesulfonic acid. [5] The addition of methylamine to sodium vinylsulfonate in aqueous solution gives N-methyltaurine in 85% yield after acidification with acetic acid. [6] The purification of the crude product and preparation of the N-methyltaurine can also be accomplished by passage of the sodium salt solution through a cation exchange resin in its H form and then through an anion exchange resin in its OH form. [7] The reaction of sodium isethionate with methylamine in water at high temperature and pressure yields the sodium salt of N-methyltaurine [8]

N-Methyltaurin Syntheseweg.svg

which yields pure N-methyltaurine upon saturation with CO2 and removal of the precipitated sodium bicarbonate. [9]

Properties

N-Methyltaurine is a white powdery solid which is readily soluble in water.

Use

N-Methyltaurine (or its sodium salt) is used as a polar head group in surfactants from the class of taurides (acylaminoethanesulfonates), sometimes also called methyltaurates. The Taurides are characterized by excellent foaming - even in the presence of oil and skin fats - and foam stability, with good skin compatibility and broad pH stability. [10] The market breakthrough for N-methyltaurine as a hair restorer is still pending.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Taurine</span> Aminosulfonic acid not incorporated into proteins

Taurine, or 2-aminoethanesulfonic acid, is a non-proteinogenic naturally occurred amino sulfonic acid that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word "surfactant" is a blend of surface-active agent, coined c. 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.

<span class="mw-page-title-main">Sarcosine</span> Chemical compound

Sarcosine, also known as N-methylglycine, or monomethylglycine, is a amino acid with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

<i>N</i>-Methylethanolamine Chemical compound

N-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid. It is an intermediate in the biosynthesis of choline.

<span class="mw-page-title-main">Ion-exchange resin</span> Organic polymer matrix bearing ion-exchange functional groups

An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange. It is an insoluble matrix normally in the form of small microbeads, usually white or yellowish, fabricated from an organic polymer substrate. The beads are typically porous, providing a large surface area on and inside them where the trapping of ions occurs along with the accompanying release of other ions, and thus the process is called ion exchange. There are multiple types of ion-exchange resin, that differ in composition if the target is an anion or a cation. Most commercial resins are made of polystyrene sulfonate, followed up by polyacrylate.

<span class="mw-page-title-main">Peptide synthesis</span> Production of peptides

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis in living organisms occurs in the opposite direction.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

<span class="mw-page-title-main">Isethionic acid</span> Chemical compound

Isethionic acid is an organosulfur compound containing an alkylsulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833. It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. It is most commonly available in the form of its sodium salt.

Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. It is typically performed during the work-up step following a chemical synthesis to purify crude compounds and results in the product being largely free of acidic or basic impurities. A separatory funnel is commonly used to perform an acid-base extraction.

<span class="mw-page-title-main">Polyaspartic acid</span> Chemical compound

Polyaspartic acid (PASA) is a biodegradable, water-soluble condensation polymer based on the amino acid aspartic acid. It is a biodegradable replacement for water softeners and related applications. PASA can be chemically crosslinked with a wide variety of methods to yield PASA hydrogels. The resulting hydrogels are pH-sensitive such that under acidic conditions, they shrink, while the swelling capacity increases under alkaline conditions.

<span class="mw-page-title-main">Sodium 2-hydroxyethyl sulfonate</span> Chemical compound

Sodium 2-hydroxyethyl sulfonate is the sodium salt of 2-hydroxyethane sulfonic acid, it is used as a hydrophilic head group in washing-active surfactants, known as isethionates (acyloxyethanesulfonates) due to its strong polarity and resistance to multivalent ions. It is being studied as a high production volume chemical in the "High Production Volume (HPV) Chemical Challenge Program" of the US Environmental Protection Ministry EPA.

<i>N</i>-Hydroxyphthalimide Chemical compound

N-Hydroxyphthalimide is the organic compound with the formula C6H4(CO)2NOH. A white or yellow solid, it is a derivative of phthalimide. The compound is as a catalyst in the synthesis of other organic compounds. It is soluble in water and organic solvents such as acetic acid, ethyl acetate and acetonitrile.

N-Oleoylsarcosine (Sarkosyl O) is an amphiphilic oleic acid derivative having a sarcosine head group (N-methylglycine) which is used as a water-in-oil emulsifier and corrosion inhibitor.

<span class="mw-page-title-main">Ethyl cyanohydroxyiminoacetate</span> Chemical compound

Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity and suppresses base catalyzed side reactions, in particular racemization.

<span class="mw-page-title-main">2,2',2''-Nitrilotriacetonitrile</span> Chemical compound

Nitrilotriacetonitrile (NTAN) is a precursor for nitrilotriacetic acid, for tris(2-aminoethyl)amine and for the epoxy resin crosslinker aminoethylpiperazine.

1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3) into hydrophobic compounds possessing nucleophilic functional groups, for example hydroxy groups (as in the case of β-cyclodextrin) or amino groups (as in the case of polymethine dyes). In such, the sulfobutyl group is present as neutral sodium salt and considerably increases the water solubility of the derivatives.

<span class="mw-page-title-main">3-Dimethylaminoacrolein</span> Chemical compound

3-Dimethylaminoacrolein is an organic compound with the formula Me2NC(H)=CHCHO. It is a pale yellow water-soluble liquid. The compound has a number of useful and unusual properties, e.g. it "causes a reversal of the hypnotic effect of morphine in mice" and has a "stimulating effect in humans".

<span class="mw-page-title-main">Taurates</span>

Taurates (or taurides) are a group of mild anionic surfactants. They are composed of a hydrophilic head group, consisting of N-methyltaurine (2-methylaminoethanesulfonic acid) and a lipophilic residue, consisting of a long-chain carboxylic acid (fatty acid), both linked via an amide bond. The fatty acids used could be lauric (C12), myristic (C14), palmitic (C16) or stearic acid (C18), but mainly mixtures of oleic acid (C18:1) and coconut fatty acid (C8 – C18) are used. Besides sodium, no other counterions play a relevant role (these could be e. g. ammonium or other alkali or alkaline earth metals).

Isethionates are esters of long-chain aliphatic carboxylic acids (C8 – C18) with isethionic acid (2-hydroxyethanesulfonic acid) or salts thereof, such as ammonium isethionate or sodium isethionate. They are also referred to as acyl isethionates or acyloxyethanesulfonates.

<span class="mw-page-title-main">Trisodium dicarboxymethyl alaninate</span> Chemical compound

Trisodium N-(1-carboxylatoethyl)iminodiacetate, methylglycinediacetic acid trisodium salt (MGDA-Na3) or trisodium α-DL-alanine diacetate (α-ADA), is the trisodium anion of N-(1-carboxyethyl)iminodiacetic acid and a tetradentate complexing agent. It forms stable 1:1 chelate complexes with cations having a charge number of at least +2, e.g. the "hard water forming" cations Ca2+ or Mg2+. α-ADA is distinguished from the isomeric β-alaninediacetic acid by better biodegradability and therefore improved environmental compatibility.

References

  1. Kalaitzis, John A; Almeida Leone, Priscila de; Quinn, Ronald J; Healy, Peter C (2003). "Zwitterionic 2-(methylamino)ethanesulfonic acid". Acta Crystallographica Section E. 59 (5): o726. doi:10.1107/S160053680300895X. hdl: 10072/6334 .
  2. B. Lindberg, Methylated Taurines and Choline Sulfate in Red Algae, Acta Chem. Scand., 9, 1955, pp 1323 – 1326.
  3. E.W. Flick, Cosmetic Additives: An Industrial Guide, Noyes Publication, Park Ridge, New Jersey, 1991, ISBN   0-8155-1255-4, S. 352.
  4. Dittrich, Eugen (1878). "Ueber Methyltaurin und die Bildung von Methyltaurocyamin und Taurocyamin". Journal für Praktische Chemie. 18: 63–78. doi:10.1002/prac.18780180102..
  5. Schick, John W; Degering, Ed. F (1947). "Synthesis of Taurine and N-Methyltaurine". Industrial & Engineering Chemistry. 39 (7): 906. doi:10.1021/ie50451a024..
  6. US 7049464,Kimura, Takuhiro; Tani, Tsutomu& Miyahara, Reiji,"Process for producing of an aminoalkylsulfonic acid and a method of salt exchange for a salt thereof",published 2006-05-23, assigned to Wako Pure Chemical Industries, Ltd.
  7. US 2693488,Sexton, Arthur R.,"Purification of amino alkane sulfonic acids by ion exchange",published 1954-11-02, assigned to The Dow Chemical Co.
  8. US 1932907,Nicodemus, Otto&Schmidt, Walter,"Process of preparing aminoalkylsulphonic acids",published 1933-10-31, assigned to I.G. Farbenindustrie AG
  9. DE 1122540,Elbel, Eberhard; Kaltenhaeuser, Herbert& Beck, Herwig,"Verfahren zur Herstellung von reinem N-Methyltaurin [Process for the production of pure N-methyltaurine]",published 1962-01-25, assigned to Farbwerke Hoechst AG
  10. Clariant-Broschüre: Mild Surfactants, (pdf; 801 kB)